diff --git a/surfsense_backend/app/indexing_pipeline/document_persistence.py b/surfsense_backend/app/indexing_pipeline/document_persistence.py
index f9be92fe6..d7810e516 100644
--- a/surfsense_backend/app/indexing_pipeline/document_persistence.py
+++ b/surfsense_backend/app/indexing_pipeline/document_persistence.py
@@ -10,12 +10,22 @@ from app.db import Document, DocumentStatus
 async def rollback_and_persist_failure(
     session: AsyncSession, document: Document, message: str
 ) -> None:
-    """Roll back the current transaction, refresh the document, and persist a failed status."""
-    await session.rollback()
-    await session.refresh(document)
-    document.updated_at = datetime.now(UTC)
-    document.status = DocumentStatus.failed(message)
-    await session.commit()
+    """Roll back the current transaction and best-effort persist a failed status.
+
+    Called exclusively from except blocks — must never raise, or the new exception
+    would chain with the original and mask it entirely.
+    """
+    try:
+        await session.rollback()
+    except Exception:
+        return  # Session is completely dead; nothing further we can do.
+    try:
+        await session.refresh(document)
+        document.updated_at = datetime.now(UTC)
+        document.status = DocumentStatus.failed(message)
+        await session.commit()
+    except Exception:
+        pass  # Best-effort; document will be retried on the next sync.
 
 
 def attach_chunks_to_document(document: Document, chunks: list) -> None:
diff --git a/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py b/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py
index 2fff9358c..70c25fcfe 100644
--- a/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py
+++ b/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py
@@ -135,7 +135,6 @@ class IndexingPipelineService:
                 return []
             except TRANSIENT_DB_ERRORS as e:
                 log_doc_skipped_db(ctx, e)
-                await self.session.rollback()
             except Exception as e:
                 log_doc_skipped_unknown(ctx, e)
                 continue
@@ -207,14 +206,14 @@ class IndexingPipelineService:
             log_permanent_llm_error(ctx, e)
             await rollback_and_persist_failure(self.session, document, llm_permanent_message(e))
 
-        except EMBEDDING_ERRORS as e:
-            log_embedding_error(ctx, e)
-            await rollback_and_persist_failure(self.session, document, embedding_message(e))
-
         except RecursionError as e:
             log_chunking_overflow(ctx, e)
             await rollback_and_persist_failure(self.session, document, PipelineMessages.CHUNKING_OVERFLOW)
 
+        except EMBEDDING_ERRORS as e:
+            log_embedding_error(ctx, e)
+            await rollback_and_persist_failure(self.session, document, embedding_message(e))
+
         except FATAL_DB_ERRORS as e:
             log_db_fatal_error(ctx, e)
             raise
diff --git a/surfsense_backend/app/indexing_pipeline/pipeline_logger.py b/surfsense_backend/app/indexing_pipeline/pipeline_logger.py
index c0df3f130..771b50645 100644
--- a/surfsense_backend/app/indexing_pipeline/pipeline_logger.py
+++ b/surfsense_backend/app/indexing_pipeline/pipeline_logger.py
@@ -88,7 +88,7 @@ def log_doc_skipped_unknown(ctx: PipelineLogContext, exc: Exception) -> None:
 
 
 def log_batch_aborted(ctx: PipelineLogContext, exc: Exception) -> None:
-    _safe_log(logger.critical, LogMessages.BATCH_ABORTED, ctx, error=exc)
+    _safe_log(logger.critical, LogMessages.BATCH_ABORTED, ctx, exc_info=exc, error=exc)
 
 
 def log_race_condition(ctx: PipelineLogContext) -> None:
@@ -110,15 +110,15 @@ def log_retryable_llm_error(ctx: PipelineLogContext, exc: Exception) -> None:
 
 
 def log_permanent_llm_error(ctx: PipelineLogContext, exc: Exception) -> None:
-    _safe_log(logger.error, LogMessages.LLM_PERMANENT, ctx, error=exc)
+    _safe_log(logger.error, LogMessages.LLM_PERMANENT, ctx, exc_info=exc, error=exc)
 
 
 def log_embedding_error(ctx: PipelineLogContext, exc: Exception) -> None:
-    _safe_log(logger.error, LogMessages.EMBEDDING_FAILED, ctx, error=exc)
+    _safe_log(logger.error, LogMessages.EMBEDDING_FAILED, ctx, exc_info=exc, error=exc)
 
 
 def log_chunking_overflow(ctx: PipelineLogContext, exc: Exception) -> None:
-    _safe_log(logger.error, LogMessages.CHUNKING_OVERFLOW, ctx, error=exc)
+    _safe_log(logger.error, LogMessages.CHUNKING_OVERFLOW, ctx, exc_info=exc, error=exc)
 
 
 def log_db_transient_error(ctx: PipelineLogContext, exc: Exception) -> None:
@@ -126,7 +126,7 @@ def log_db_transient_error(ctx: PipelineLogContext, exc: Exception) -> None:
 
 
 def log_db_fatal_error(ctx: PipelineLogContext, exc: Exception) -> None:
-    _safe_log(logger.critical, LogMessages.DB_FATAL, ctx, error=exc)
+    _safe_log(logger.critical, LogMessages.DB_FATAL, ctx, exc_info=exc, error=exc)
 
 
 def log_unexpected_error(ctx: PipelineLogContext, exc: Exception) -> None: